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CHEBI:5000 - fenfluramine

ChEBI IDCHEBI:5000
ChEBI Namefenfluramine
Stars
DefinitionA secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.
Secondary ChEBI IDCHEBI:239434
Last Modified22 February 2017
DownloadsMolfile
FormulaC12H16F3N
Net Charge0
Average Mass231.261
Monoisotopic Mass231.12348
SMILESCCNC(C)Cc1cccc(C(F)(F)F)c1
InChIInChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3
InChIKeyDBGIVFWFUFKIQN-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
serotonergic agonist  An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
serotonin uptake inhibitor  A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
Applications:
serotonergic agonist  An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
serotonin uptake inhibitor  A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
appetite depressant  Any agent that is used to decrease appetite.
ChEBI Ontology
Outgoing Relation(s)
fenfluramine (CHEBI:5000) has role appetite depressant (CHEBI:50507)
fenfluramine (CHEBI:5000) has role serotonergic agonist (CHEBI:35941)
fenfluramine (CHEBI:5000) has role serotonin uptake inhibitor (CHEBI:50949)
fenfluramine (CHEBI:5000) is a (trifluoromethyl)benzenes (CHEBI:83565)
fenfluramine (CHEBI:5000) is a secondary amino compound (CHEBI:50995)
Incoming Relation(s)
fenfluramine hydrochloride (CHEBI:59729) has part fenfluramine (CHEBI:5000)
(R)-fenfluramine (CHEBI:521051) is a fenfluramine (CHEBI:5000)
(S)-fenfluramine (CHEBI:439329) is a fenfluramine (CHEBI:5000)
IUPAC Name 
N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine
INNs  Source
fenfluraminumChemIDplus
fenfluramineChemIDplus
Synonyms  Source
FenfluramineKEGG COMPOUND
N-ethyl-1-(3-(trifluoromethyl)phenyl)propan-2-amineChEMBL
Ethyl-[1-methyl-2-(3-trifluoromethyl-phenyl)-ethyl]-amineChEMBL
1-(m-trifluoromethyl-phenyl)-2-ethylaminopropaneChemIDplus
2-ethylamino-1-(3-trifluoromethylphenyl)propaneChemIDplus
N-ethyl-α-methyl-3-trifluoromethylphenethylamineNIST Chemistry WebBook
Manual XrefsDatabases
C06996KEGG COMPOUND
D07945KEGG DRUG
DB00574DrugBank
US3198833Patent
HMDB0015322HMDB
FenfluramineWikipedia
1150DrugCentral
Registry NumbersSources
Reaxys:2109374Reaxys
CAS:458-24-2KEGG COMPOUND
CAS:458-24-2ChemIDplus
CAS:458-24-2NIST Chemistry WebBook
Citations